Potassium Hydroxide → 1-(2',3'-Dimethyl-4'-methoxyphenoxy)-3-(tert.-butylamino)-2-propanol

HRID 2198859Notes

Reaction equation

[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[OH:11].[C:12]([N:16]1[CH2:19][CH:18]([OH:20])[CH2:17]1)([CH3:15])([CH3:14])[CH3:13].[OH-].[K+]>Cl>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[O:11][CH2:17][CH:18]([OH:20])[CH2:19][NH:16][C:12]([CH3:13])([CH3:14])[CH3:15]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 9.1 parts of 2,3-dimethyl-4-methoxyphenol, 6.5 parts of 1-(tert.-butyl)-3-azetidinol and 0.3 part of potassium hydroxide was heated under nitrogen gas at 140° C. for 8 hours with agitation. The reaction product was dissolved in 100 parts of 2 N-hydrochloric acid aqueous solution and washed twice with 100 parts of ether. The water layer was made alkaline with 4 N-sodium hydroxide aqueous solution, and the resulting crystals were recovered by filtration and dried. Then the crystals were dissolved in 100 parts of ether and decolored. The decolored liquid was concentrated and allowed to cool. As a result, 10.2 parts of 1-(2',3'-dimethyl-4'-methoxyphenoxy)-3-(tert.-butylamino)-2-propanol melting at 73°-75° C. were obtained. The yield was 72.5%. The results of infra-red spectrum analysis and nuclear magnetic resonance analysis of the product are as follows:

Workup

washwashed twice with 100 parts of ether
filtrationthe resulting crystals were recovered by filtration
customdried
dissolutionThen the crystals were dissolved in 100 parts of ether
concentrationThe decolored liquid was concentrated
temperatureto cool

Sources & evidence

ORD record: ord-de91f1af25ca4db8b7fe0ee53b575ded
Source dataset: uspto-grants-1982_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04360464

Reaction notes

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